Top 10 Funniest Moments in Pro Wrestling History

There’s a reason they call it sports entertainment. Professional wrestling is able to evoke many emotions from its fans. Laughter is one of them. It’s not always intentional, but one cannot dispute that comedy is a fun component of wrestling. While it can’t be the dominant genre of the profession, a little comedy sprinkled into the program is golden when done right. Sometimes comedy just happens in wrestling as things don’t always go as planned. Whether it’s a wrestler butchering a line or missing a spot, funny moments can happen on a whim. Sometimes comedy just comes naturally for a wrestler, as they’re able to incorporate it into their promos or matches while still not losing their hold on the crowd. The best example is the Rock, who got you pumped up and laughing with any promo. Stone Cold‘s antics with Mr. McMahon never failed to produce a few laughs. Mick Foley was just so goofy, yet tough. Heck, even the gold medalist Kurt Angle was a riot when you think about it. Intentional or not, here are the top 10 funniest moments in pro wrestling history.

10.The Rock Ends the Mr. McMahon Kiss My Ass Club

You can say what you want about the Vince McMahon Kiss My Ass Club. It was disgusting, low-brow, juvenile, etc… But, The Rock putting an end to it was priceless. Having beaten McMahon and Kurt Angle in a tag team match with Trish Stratus, the stipulation was that McMahon would have to pucker up and kiss the Brahma Bull’s backside.

The Rock would tease making Vince kiss Bull’s behind, only to pull out those whom Vince had humiliated from backstage. First it looked like he’d be puckering up for good old J.R. It looked for a while like Vince would get off the hook and kiss Trish Stratus’s derriere. Finally The Rock brought out Rikishi. After a Rock Bottom on McMahon, The Rock shoved McMahon’s face into the enormous rear end of Rikishi. Jim Ross yelled, “There is a God in this world!” and McMahon looked like he was losing his lunch. You won’t see another billionaire do this on television.

9.The Rock Sings for Sacramento

It should come as no surprise that The Rock will make several appearances on this list. The Rock was entertaining both as a heel and a face, but one run that wasn’t long enough was his villainous stint playing a Hollywood sellout. His sheer arrogance and mockery of the millions was comedy gold. Even though he was a heel and trashing fans in his promos, the fans couldn’t help but laugh at The Rock’s antics. Boos were mixed with cheers and laughs, because he was just so quick-witted and found a whole new way to interact with the fans.

This was perhaps best illustrated when he held a ‘Rock Concert’ for the city of Sacramento in the buildup to his match with Steve Austin at WrestleMania XIX. The Rock sang songs mocking Sacramento’s fans and his opponent Stone Cold. You hear boos and laughs coming from the crowd and see that Austin is doing his best not to burst out in laughter backstage. “Sacramento, I won’t stay, but I’ll be sure to come back when the Lakers beat the Kings in May!” The Rock drew heat, but had the crowd in the palm of his hand the whole time.

8.DX Impersonates the McMahons

D-Generation X’s feud in 2006 with the McMahons faced a mixed reception by wrestling pundits, but it can’t be disputed that DX created an abundance of funny moments at the expense of Mr. McMahon. Perhaps the best moment of the feud came when Triple H impersonated his own father-in-law while Shawn Michaels then impersonated Shane-O-Mac.

The segment left you wondering, did they really just say those things? Well, Triple H sure performed the Mr. McMahon walk with gusto and HBK went over the top in dancing like Shane McMahon. While many loved DX impersonating the Nation of Domination back in 1998, I personally enjoyed this one more. Partly because DX had the benefit of impersonating the bosses, which is always a plus.

7.The Shockmaster Debuts

Too bad the WCW moments on this list are unintentional. Talk about a wrestler’s push being over before it got started. Fred Ottman was known as Tugboat in the World Wrestling Federation, but made his debut in WCW in 1993. He was going to be thrown in a tag team match with some of WCW’s most popular stars in Sting, Davey Boy Smith and Dustin Rhodes. The four would team up against a team of heels, including Vader, Sid Vicious and Harlem Heat.

When the team of heels demanded to know who the mystery partner was for Sting’s team, Sting built up the debut of the Shockmaster perfectly. “All I have to say is, our partner is going to “shock” the world, because he is none other than…The Shockmaster!!” The camera cut to a fire blast, a thin wall broke and a big guy in a sparkling storm trooper-type helmet fell through the wall and lost his headgear. You could hear the reactions of the wrestlers on camera, including Davey Boy saying, ‘he fell flat on his ass!’

Word was WCW had big plans with the gimmick, but this incident clearly derailed everything. However, fall or no fall, something tells me a guy in a glittered storm trooper helmet would’ve never been taken seriously anyway.

6.Austin Appreciation Night / Milk Truck

While Austin driving a beer truck to the ring could’ve easily taken a top spot on this list, I personally enjoyed Kurt Angle driving a milk truck to the ring to soak Austin and the Alliance members even more.

Austin was portraying a paranoid, insecure Stone Cold. Having retained his title the night before at SummerSlam, he was thrown an appreciation night by the Alliance. Kurt Angle then drove a milk truck to the ring and proceeded to whip milk cartons at the wrestlers and spray a milk hose. Everything about this segment worked. Angle’s intensity when whipping the milk, Stone Cold’s reaction and Jim Ross’s enthusiastic commentary, “The billion-dollar princess has become a dairy queen!”

5.Booker T calls Hulk Hogan the “N” Word

Whoops. Do you think Booker T would like a mulligan on this promo? This has arguably been made even more famous in the internet age. Booker T is well regarded as one of the WCW’s all-time best talents and was a great performer for many years in the wrestling business. This one will stand by him forever, though.

Cutting an intense promo on Lex Luger and Hulk Hogan, Booker T committed one of wrestling’s funniest bloopers, exclaiming, “Hulk Hogan, we comin’ for you, n****!” As soon as the words left his mouth, you could see Booker T shake his head and Sensational Sherri laughing while trying to coax Booker.

4.Stone Cold Attacks Booker T at a Grocery Store

There’s just something about Stone Cold attacking someone that makes it funny. Props to the grocery store that allowed the WWE to come in and tear up the place. Austin was chasing down Booker T for costing him the title at Vengeance 2001 and the chase led Austin to the grocery store. After Booker T attacked a Stone Cold look-a-like, Austin went to town on Booker hitting him with oranges, flour, squirting him with mustard and causing as much damage as possible to the store.

My personal favourite is Austin singing, “When the moon hits your eye, like a big pizza pie, that’s amore!” and proceeding to nail Booker with a pizza crust. I never thought I’d hear someone with a Texas accent singing that.

3.The Rock Insults Hell-In-A-Cell Opponents

I don’t know about you, but I could spend a whole day watching The Rock‘s promos. One that stands out was The Rock making fun of all five of his opponents prior to the six-man Hell-In-A-Cell match at Armageddon 2000.

Whether they were heels or faces, The Rock managed to zing them all within four minutes. Every line worked, as The Rock’s facial expressions, delivery and timing all came together and went over great with the audience. Many arguments can be made for many more of The Rock’s promos to be on this list. This promo exemplified all of The Great One’s ability and how he could get the fans going in any direction he wanted.

2.Stone Cold Attacks Mr. McMahon at the Hospital

For a period of time, you asked yourself every Monday, what is Austin going to do to Vince McMahon this week? If I had to go with my personal favourite, it would be Stone Cold posing as a doctor and attacking McMahon at the hospital. The highlight of the segment for me was the noise of the bedpan when Austin bashed it off of McMahon’s head. The sound was so comedic in and of itself.

Austin proceeded to attack McMahon’s injured foot and McMahon yelled at the top of his lungs in pain. This segment was as entertaining as they come and segments like these were a big reason the WWE reached its peak in popularity and eventually beat out WCW in the Monday Night ratings war.

1.Mankind Presents “This Is Your Life” to The Rock

I’ll justify this choice by pointing out the fact that it was the highest-rated segment in WWE history with an 8.4 rating. Wrestling rating are never that high, and the only thing that could explain the jump was that non-wrestling fans were watching this as well.

Mick Foley‘s creative mind and The Rock‘s charisma formed the perfect storm in making this moment an all-time great. The Rock ‘n’ Sock Connection was a great combination of the goofy, good-natured Mankind and the brash, arrogant Rock, in which Mankind was seeking friendship from the Brahma Bull. Mankind pulled out all the stops, celebrating the Rock’s birthday over four months late and bringing out The Rock’s home-ed teacher, high school coach and even his high school sweetheart. The Rock pointed out the mean things they did to him, belittled them in a way only The Rock could and got them booed out of the arena. Mankind just couldn’t catch a break. The ratings the segment received were unprecedented and will likely never be matched again.